


Yes, Master

by Nachsie



Series: Straight up porn (with adorable plots!) - One Shots [25]
Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Assassins & Hitmen, Alternate Universe - BDSM, Alternate Universe - Human, Alternate Universe - No Powers, Anal Fingering, Anal Sex, Angst and Fluff and Smut, BDSM, Boss Castiel (Supernatural), Bottom Dean Winchester, Castiel/Dean Winchester BDSM, Dean Winchester Likes It Rough, Dean Winchester Topping From the Bottom, Dean in a pink satin thong, Eventual Happy Ending, Eventual Relationships, Falling In Love, Fetish, Fluff and Smut, Gay Sex, Hitman Sam Winchester, Light BDSM, M/M, Mafia Boss Castiel, Master Castiel (Supernatural), Master/Pet, Office Blow Jobs, Office Sex, One Shot, Oral Sex, Pet Dean Winchester, Pink Panties, Pink Satin Thong, Porn, Porn With Plot, Porn with Feelings, Rough Kissing, Rough Oral Sex, Secret Relationship, Semi-Public Sex, Shameless Smut, Smut, Top Castiel/Bottom Dean Winchester, Watching, hitman dean winchester, pink thong
Language: English
Status: Completed
Published: 2020-12-08
Updated: 2020-12-08
Packaged: 2021-03-10 00:13:45
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,140
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27961346
Author URL: https://archiveofourown.org/users/Nachsie/pseuds/Nachsie
Summary: When a mafia boss tells you to come to his office, you do. When he tells you to get on your knees, you do. When he tells you to unzip his pants, you do...happily.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Series: Straight up porn (with adorable plots!) - One Shots [25]
Series URL: https://archiveofourown.org/series/220667
Comments: 7
Kudos: 189





	Yes, Master

Gripping his brass knuckles as blood slid down from his hands, blood dripping onto the concrete floor already soaked in blood. The gagged man passing in and out of consciousness glanced up to see the man torturing him. Everyone knew who this man who held him was. The biggest gang, the Angels, best right-hand man. Dean Winchester. 

He was the one they sent to handle the messes, the one that always got the job done without breaking a sweat or getting a drop of blood on him. The man knew he wasn’t getting out of this alive. The man knew if he spoke what his torturer wanted, he was dead from his own gang, but if he didn’t...He would be killed slower. At least his gang would just fucking kill him. 

Dean? No, he took his fucking time. He made you beg to die and then...refused. Making you suffer even more. Dean’s cold fucking dead eyes baring into him as he inflicted pain only fucking sadist could think of. 

Dean was cool and collected, all unable to tell what he was thinking till he did it. Dean was a man everyone feared. Hell, he was the Cerberus to the angels. No one could _handle_ Dean Winchester. Dean _handled_ you. If Dean was after you, you only hoped you could kill yourself before he got there. 

In fact, the man tied up in here only lasted fifteen minutes, ending up with three missing fingers broken and cut off at different joints. A face mauled by the brass knuckles with sharp spikes at the end and a majority of his ribs broken. 

He knew he wouldn’t last long.

No one would last long with Dean Winchester.

That fucking man...was a _monster._

It was a wonder how anyone controlled the beast. 

Especially since anyone would jump at the opportunity to own him. To have THE Dean Winchester on their sides. They would pay anything, give anything, DO anything. However, no matter what he was offered he refused...before sending a message to their boss that he wasn’t interested. Sending their heads to them in a decorated gifted box. 

Everyone wondered how the Angels had bought Dean’s loyalty.

Loyalty was hard to find.

Men _like_ Dean were hard to find.

Everyone feared the men with **_nothing_ ** to lose.

One had to wonder what the Angels gave to Dean. 

He wanted for nothing.

He couldn’t be bought.

What did Dean Winchester value?

If not Money, blood, or power then what?

“Tell me what I want to know,” Dean spoke walking around the man who was shaking and whimpering from his injuries. 

Dean Winchester’s green eyes stared coldly as he moved to land another punch but the man screamed behind the gag nodding in fear that he would talk. Dean reached over annoyed pulling the gag from his mouth. 

“Scream and I’ll pull your teeth out, one by one,” Dean spoke as he circled him. “Where is the money?”

“My boss is going to kill me-” The man begged as Dean moved to put the gag in again. “BUT! WAIT! BUT!” Dean stopped.

“Where. Is. The. Money?” Dean spoke slowly and with purpose. 

“Look, they didn’t have time to take the money they stole from your boss far.” The man choked. “They didn’t have time at all. His men were there faster than any of us expected. We thought we had more time.”

“My patience is running _thin_.” Dean breathed cleaning his brass knuckles of blood. The man watched Dean clean them with care. “The blood makes them a bit slippery. If I plan to make you eat out of a straw for the rest of your life, I need to hit with purpose and accuracy. I would hate to kill you accidentally, you know?” Dean made a punching motion before laughing throwing his head back like it was funny. The man went pale with fear. 

What a sick FUCK.

“Where’s the money?!” Dean yelled out as the man whimpered. Dean leaned into him standing in front of him getting in his face before softly whispering. “...tell me, and I’ll put you out of your misery...It will be so quick...you can rest. Don’t you want to rest?” 

This wasn’t with care or concern.

It was manipulation…

...and he bought into it.

The man cried not wanting any more pain as he nodded again. 

“Okay, Okay. I’ll tell you.” The man sobbed whining and snotty as Dean looked down at him. “Look. They couldn’t go with the plan. We dumped the backpacks of money into a mailbox on Impala road before you caught us. Please...Let me die.” Dean eyed him determining if it was a lie before he pulled back. Dean slowly lowering his brass knuckles to the bloody medical tray where all his torture devices were, just as the door opened to see his younger brother standing there.

“Boss wants you,” Sam spoke moving to take the extra chair to sit in front of the man. “I’ll take over,” Dean said nothing barely casting a glance at the man.

“No need. Release him. We are done.” Dean commented moving past them as the man looked on in fear. 

“NO! Please! They will kill me slowly for snitching!” The man choked. “You PROMISED!”

“Well, I lied.” Dean mocked coldly as he walked away leaving the man to his fate.

___________________________________________________________________________

  
  
  
  
  
  
  
  
  


Dean Winchester pushed open the Boss’s office doors, his boss glancing up as he crossed his fingers leaning back in his chair eyeing the assassin. Dean didn’t have to be told to close the doors to secure them. Standing staring at his boss, taking in his cocky blue eyes of power. The smirk Dean recognized more than breathing. Castiel Novak. The most powerful man in the underground world, in control of so much money, power- Castiel was closer to the devil than man. He owned your soul and held your life in his hands before you even realized it was. 

Everyone feared the man with **_everything_** to lose. 

No words were exchanged for a long time before his boss raised his fingers coaxing him over with a small gesture. 

“Come.” His boss spoke in his deep rough voice as Dean walked over without argument moving to the mafia boss’s chair before he dropped slowly to his knees in front of him. Dean stared up at Castiel with his lips slightly parted. The boss ran his thumb against Dean’s bottom lip.

“Have you been good for your master?” Castiel murmured as Dean slowly nodded. “Good enough to deserve a treat?” Castiel slid his thumb into Dean’s parted lips as Dean stared up at him with those big green eyes nodding as he slowly licked at the thumb. “...Then you may have your treat.” Castiel pulled his thumb away from Dean’s mouth as Dean lightly panted turned on. Dean didn’t hesitate to obey as his mouth moved to mouth at the fabric slacks hiding Castiel’s cock from him. Castiel didn’t make a noise but then again he never did. He reacted to every little touch Dean did to him, keeping his moans or pants from Dean till he _earned_ them. 

Dean glanced up at him all so desperate for the flesh under his pants, but he took his time. Slowly wetting the bulge with his salvia before he moved to unbutton and slid down his zipper. He loved it when Castiel got hard from his mouth alone. Dean never moved directly to the cock though, he still needed to earn it. Dean moved his mouth to his boxers wrapping his mouth around the outline making sure his tongue slipped through the slit of the fabric to taste him. 

He couldn’t be too eager.

He needed to make sure his master permitted him to take his cock. 

_______________________________________________________________________

  
  
  
  
  
  
  
  
  
  


Castiel watched him amused that his pet took his time with him, Dean always seemed to make sure Castiel was fully satisfied before sex. How particularly blessed was he to have such a loyal dog. His pet. 

When he had found Dean, it was just Sam and Dean. Freelance. Sure Sam was more the brains but Dean was...Dean was the force behind them. Everyone had tried to get the Winchesters. They wanted nothing. They didn’t _need_ anything. They were famous enough to freelance forever to get money or power when they needed it. Everyone else had tried and failed. Though Castiel was smart. Going to the more logical brother first. Sam was on board with simple logic when Castiel approached him with what the gang would offer the genius. 

...But Dean, he was the tricky one.

...he didn’t seem to care about anything.

Castiel had to fight for Dean.

What did a man with all the power want more than anything?

He remembered when he stared into the green eyes that refused him. Remembered how cold Dean looked as he told him no. He looked like he had died so long ago. No life in those eyes…

...but Castiel told him he would. 

Told him he could get Dean Winchester on his knees and submit. Stating when he did Dean had to agree to be loyal to the Angels. 

Dean agreed amused by the cockiness...but that cockiness ended with Dean pulling Castiel’s cock from his zipper and sucking at Castiel’s cock like a good boy. Just a couple of words. 

What do you give a man who has everything?

The weight of the world off his shoulders…

Castiel had a hunch, once alone taking Dean’s hair in his hands. So quickly Dean couldn’t react as Castiel pulled his hair back slamming Dean’s front into the brick wall. Dean’s breath hitched at the idea of someone pinning him. Castiel pressed his bulge against Dean’s ass making Dean tense sucking in the air at the touch. That’s when...Castiel knew he won.

_“Be a good boy and suck off your master.”_ Castiel hissed into his ear. _“And I’ll reward you with my cock.”_

Castiel bit at Dean’s ear as he let go of Dean forcing Dean to face him. Dean stared into his eyes for a long moment of silence. Castiel thought for a moment he misread him. No reaction to his command... before Dean fell to his knees moving with shaking from excitement and...his own desire to submit. His hands moved to unzip and pull Castiel from his restraints. Castiel could only close his eyes in satisfaction feeling those plump virgin lips mouth his tip tasting cock for the first time. 

___________________________________________________________________________

  
  
  
  
  
  
  
  


Castiel thoughts returned to Dean when Dean had pulled his cock out of his zipper mouthing at the sides his fingers rubbing at his sack massaging them giving them the attention they deserve. Dean’s lips smeared pre-cum over them as Dean’s tongue teased the tip. Castiel let out a satisfied moan. Earning Dean’s eyes to light up as he paused slightly as Castiel nodded at Dean.

Dean stood happily unbuckling his pants and kicking off his shoes. Before letting his pants fall to the floor as he slid out of them. Castiel took in the pink satin thong Castiel had bought Dean. Castiel always bought Dean little gifts like these when he was extra good. Dean has been extra good lately. Coming when allowed. Being open to new experiences and positions Dean never tried before. Dean especially loved the pink handcuffs permanently attached to Castiel’s bed frame. 

Dean wanted to get Dean a ball gag next...but he loved his mouth too much…

He knew he would never use it...not when he could gag Dean with something else. 

Dean moved to slide down the underwear but Castiel’s voice stopped him. 

“Leave it on and stay,” Castiel commanded as Dean stopped his hands before pulling them back on. Castiel watched Dean slid it back on completely. Castiel reached into his desk pulling lube from the drawer. Lathering his cock with the lube. He took his time to pleasure himself lubing it up for Dean. Dean watched swallowing before Castiel slid some lube onto his fingers. “Come.” 

Dean moved to him staring down at Castiel’s fingers, he knew the position to get lubed. Dean bent over the desk exposing his ass to him. Castiel eyed his cheeks in the satin thong, how he loved Dean in those. 

“Hold yourself open,” Castiel commanded as Dean reached back pulling his panties and cheeks away exposing himself to his master. Castiel eyed his hole taking time to enjoy his view before he slathered his lubed fingers against his hole. Dean moaned closing his eyes as Castiel took his time to slowly finger his hole. Starting with one finger. 

He loved watching Dean adjust to his fingers. 

When Dean was shaking in pleasure was his favorite time to tease him, he would slow his fingers down aiming for deeper. Castiel watching Dean take his fingers so well.

“You are used to two,” Castiel mumbled as Castiel slid in the forth. Dean whimpered as the stretching. “Now I will get you used to three.” 

“T-Three?” Dean breathed nervously.

“Breakfast, Lunch, and Dinner you shall come and present yourself to me till you can take three without hesitation. Is that understood?”

“Y-Yes, Master.” Dean panted as his eyes rolled into the back of his head at the teasing. Taking each finger as a blessing. 

Dean had never been...treated like this. His whole life, he was treated as the boss, the leader. When Dean’s mother died, Dean was only a child. Dean had to grow up early just to take care of Sam. Sam had something he would call at least sort of normal childhood. Dean’s father took to training Dean young to take over the family business. The handlers, his father would call them. The people who got everything done. No hesitation.

Dean killed his first target at eight years old, learned every torture technic by fourteen, and took over the family business when his father died at sixteen.

Sam killed his first kill was by fourteen when their father died. Men had jumped them and killed their father. The only reason they both survived was both of them fighting together. Though Dean had tried to protect Sam from the life, the life sucked Sam up all the same. Dean took on the responsibility to keep them safe and well. 

But that...is so tiring to be strong all the time.

Even if they built up their reputations along with the family name. Even becoming the monsters of the underground world. The weight only added on. He couldn’t protect Sam by trusting these men who tried to buy their loyalty. Dean couldn’t trust ANYONE. 

But...then he met Castiel. 

Dean remembered Sam telling him once again another gang has sent their men to try to convince the Winchester brothers to be theirs and only theirs. Dean was going to blow off this asshole. To tell them to crawl back to their boss and tell them to kick rocks. However. Sam had cut him off mid-thought. 

“It’s...their leader,” Sam whispered as Dean seemed surprised. “He wanted to speak to you personally.”

What kind of Leader would risk his life just to come to recruit someone?

They were _good_ , but not worth the risk of their _empire..._

Watching Castiel come in, his shoes polished, his suit an expensive light grey suit. Dean raised an eyebrow to the balls of this man to come here.

“No,” Dean stated tense, closed off, and obviously upset by this man being here. 

He didn’t like the idea of some boss coming here thinking he knew what was best for Sam...and him. Dean was in charge for a reason. The man eyed him saying nothing, standing before him accessing him. Dean felt uncomfortable under his gaze...slightly coiling inward uncomfortable by the authoritative presence in the room. Dean was great at hiding his discomfort of men taller and larger than him, Dean always attempting to be the one in charge...but Castiel smirked at him. 

“I think I can change your mind,” Castiel stated as Dean scoffed.

“Really?” Dean rolled his eyes. “You are really that confident?”

“I’m so confident that I can promise you will be on your knees and submit to me,” Castiel stated as Dean frowned. 

“Oh, you think so?” Dean laughed mockingly.

“I _know_ so.” Castiel commented before turning to his men, “Leave.” The men nodded leaving and closing the door without hesitation...and the rest was history.

_______________________________________________________________________

  
  
  
  
  
  
  


Castiel pulled his fingers out as he cleaned his fingers with the tissue paper on his desk as he took time to take in the state of Dean. 

“Pleasure yourself on my dick. I have things to do.” Castiel commented like he didn’t care...but he did. Dean knew he did. 

Dean moved to sit in his lap, pushing the thong strap to the side as he straddled him. Castiel leaned back slightly to watch. Dean was sure he lied when he said he was busy. He never worked when they were having sex, as much as he claimed to. He...was just as involved in this relationship as Dean. 

He wondered when Castiel realized he was in love with Dean as he lowered himself on his cock taking it slowly in much to Castiel’s delight. He wondered when Castiel realized Dean loved him. It just...seemed to happen. First starting as rough and desperate sex...turned into Dean living with him. 

Castiel claiming to just want his best to protect him and his property, but...Dean and Sam were the only ones who lived there as guests. They didn’t have to work unless asked to. Castiel asking Dean to share a room with him to ‘better protect’ Castiel. Only leading to more sex, kisses, and cuddling. Especially after this controlled rough sex…

Dean...really fell hard for Castiel...So fucking hard.

Dean slowly rolled his hips as Castiel watched Dean trying to fuck himself on Castiel’s cock. Moving his hips easily the way Castiel liked. Castiel liked it when Dean took his time. Quick sex made Castiel grumpy, so Dean would do it ONLY if he wanted more sex. Castiel would always be down for more to cheer himself up. 

Dean started to pick up speed slowly leaning forward to give Castiel a great look at Dean riding his cock. Castiel watched with amusement as he rested his chin in his hand watching the hitman move. Dean’s breath picking up feeling the chair start to submit to low squeaks from their movements. 

Castiel watched Dean roll his waist as he takes Castiel’s cock so well. Castiel moved to touch Dean’s scarred abs. He loved to run his hands over his abs as Dean moved on him. Sometimes, He would take Dean where he wanted. Finding Dean in the library or the hall, he would pin him against the wall and take him. Caring little if anyone saw. 

Dean loved the risk, loved to submit. Castiel wanted Dean for his skill, but he found so much more. Castiel leaned up to kiss him, Dean panting against his lips before they met. Castiel’s hands sliding up and down Dean’s body. Dean’s arms wrapped around Castiel’s shoulders as Castiel’s office phone started to ring. Castiel groaned breaking the kiss as Dean paused his rocking. 

“Don’t stop till I cum.” Castiel breathed as Dean nodded shyly, continuing to rock. Castiel casually picked up the phone annoyed at the interruption before he put it on speaker. “Speak.” 

Castiel moaned as he pulled Dean back into a rough kiss, they weren’t quiet. The person on the phone could hear their sex. Though he didn’t know who Castiel was having sex with, but it was obvious. 

“You sound busy.” The man spoke. Dean recognized the voice as Lucifer. The leader of one of the top men in the organization. 

“I’m not the one doing the work.” Castiel leaned back in the chair watching Dean slowly start to rock harder. “Tell me what you want.” 

“...” Lucifer sighed as Castiel moved two fingers into Dean’s mouth to suck, which Dean moaned to. “I have a couple terf issues with the leviathan.” 

“What have the Leviathans been up to?” Castiel asked before he moaned at Dean’s rolling hips as he moved to pull Dean’s hair. Dean let out a pleased breath rocking harder. 

“They have been attempting to take our streets by buying out the people living near it,” Lucifer spoke. “They are buying out more and more-”

“Buy the apartment building. Remind the tenants that even looking at a leviathan will get them evicted.” Castiel panted as Castiel grabbed at Dean’s hips starting to rock into him. “They will be pissy at first but when they have a hard month and need a free month. We will give it. They will submit. They will love us.” 

Castiel grabbed at Dean’s waist starting to rock up onto him. Dean moaned loudly moving to cover his mouth with Castiel’s skin. The sound of Castiel’s balls slapping up against Dean’s ass filled the room. 

“Anything else?” Castiel panted as Dean and him got close, Dean was holding onto Castiel allowing Castiel to pound him as he rocked down on his cock. Lucifer was silent as he heard small whimpers from Castiel’s sexual partner, not recognizing it as the deadly Winchester. 

“ _I-I’m cumming_ …” Dean breathed cum slowly being milked from his cock with each thrust. A gasp as Castiel slammed himself deeper getting close to his own orgasm as Dean tried to hold him. _“Fill me. Fill me.”_ Dean whimpered like a matra as Castiel pressed himself as deep as he could. Cumming deep into Dean who could only throw his head back through their orgasms. The only thing ringing through the air was their rough pants.

“...No, sir. Have a good night.” Lucifer spoke after a long time just listening before hanging up. Castiel pulled Dean close pressing their foreheads together. He loved sleeping with Dean...but these moments? Of him cuddling after sex? These were Castiel’s favorite moments. They held each other till their breaths even, Castiel just holding Dean against him. 

“I…” Castiel breathed softly as Dean’s eyes softly opened. “...I love you, Dean.” Dean opened his eyes at the words looking down at Castiel’s soft face. Castiel opened his eyes to meet Dean’s. “I want you to be mine and only mine.”

“...C-...Cas?” Dean eyed his face with surprise by the confession.

“I know...this started as a business arrangement but the idea of you holding someone like this...kissing someone like this...fucking someone like this…” Castiel breathed. “I can’t stomach it. No one should ever touch you. You’re mine, no one else's…” 

Castiel softly slid his nose affectionately against Dean’s in a small Eskimo kiss waiting for Dean’s reaction to the words. Scared he would lose Dean by the confession when he felt Dean smile cupping his face with his hands. 

“I already am…” Dean breathed with a loving smile, tears filling his eyes as he moved to kiss him before they hugged holding each other. Dean pulled back to kiss him again before Castiel’s secretary used the phone intercom. 

  
“Mister Novak, you got a meeting with the mayor in three minutes.” The secretary chewed on her gum before ending the intercom call. 

“...I should go…” Dean whispered as Castiel whined in refusal. Dean climbed off his cock, cum spilling between the thong strap. Dean moved to clean himself a bit, wiping his own cum off of him before reaching back to wipe the cum spilling out of him and onto the floor.

“Leave it.” Castiel breathed as Dean stopped smiling as he threw the napkins away letting Castiel’s cum stay. 

Sliding back into his jeans as Castiel fixed himself, sliding himself back into his pants. Dean cleaned up so well after their sexual encounters. No one could know or ever did. 

“Dean, come.” Castiel ushered him back as Dean moved to him once dressed again. Dean got onto his knees in front of Castiel automatically. Castiel grabbed Dean’s hair pulling it back as Dean moaned at the roughness. “I expect nothing else but you in my bed when I come home. Is that clear?” 

Dean nodded smiling as he eyed Castiel’s lips as Castiel smirked back moving to kiss him. Dean kissed back with care, allowing the kiss to linger before he got up to leave. 

“Love you,” Dean called as Castiel gave his ass a slap making Dean blush. He watched Dean’s ass in the tight jeans filled with his cum go like Castiel hadn’t fucked him to oblivion.

“...Love you more,” Castiel called back watching him go before his phone rang. Making himself sigh before hesitantly going back to work counting the minutes till he could go home to Dean.

  
  
  
  
  


**The end**


End file.
